Potassium Cyanide → HCID 18986921, compound

HRID 2397061Notes

Reaction equation

HRID 2397061 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH2:17][CH2:18][CH2:19]Cl)[CH:3]=1.[C-:21]#[N:22].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]([CH2:17][CH2:18][CH2:19][C:21]#[N:22])[CH:3]=1

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 10495070HCID 10495070, compound

Product 1

HCID 18986921HCID 18986921, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1.62 g of crude 4-chloro-2-(3-chloropropyl)-1-(2-phenylethoxy)benzene in 20 ml of acetonitrile, were added 681 mg of potassium cyanide and 138 mg of 18-crown-6 and heated under reflux for 11 hours. After cooling, the solvent was evaporated under reduced pressure and ethyl acetate and water were added to the residue thus obtained. Then the ethyl acetate layer was collected, washed thrice with water and a saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, 1.55 g of crude 4-[5-chloro-2-(2-phenylethoxy)phenyl]butyronitrile was obtained. This compound was not purified any more but used in the subsequent reaction.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 11 hours
  3. temperatureAfter cooling
  4. customthe solvent was evaporated under reduced pressure and ethyl acetate and water
  5. additionwere added to the residue
  6. customthus obtained
  7. customThen the ethyl acetate layer was collected
  8. washwashed thrice with water
  9. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous magnesium sulfate
  10. customAfter evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-c8e48d660a364ae889facb1129bab8ed
Source dataset
uspto-grants-1996_02
Patent number
US05495046

Reaction notes

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